For the sake of argument, I would go with the 1920s. It was just before we started destroying our built environment with almost exclusively car-oriented structures. And the Depression hadn't hit yet. Manufacturing still occured in the US. And we weren't in any major wars. Music was still taught in schools. Some of my favorite composers were still living. I'd want to be in a major city, obviously.
OTOH segregation was at its height, and women's liberation was a ways off, so that's bad. If you could wave a wand and make civil rights come earlier, the choice would be a lot easier. So you see the appeal of the 1990s.
A movie is not about what it's about; it's about how it's about it.
---Roger Ebert
Some questions cannot be answered
Who’s gonna bury who
We need a love like Johnny, Johnny and June
---Over the Rhine